Winchester Homes for Sale

Welcome to Winchester, Oregon, a hidden gem nestled in the heart of Douglas County. With its picturesque landscapes, friendly community, and a rich history dating back to the 19th century, Winchester offers a unique blend of small-town charm and modern convenience. Surrounded by the breathtaking beauty of the Umpqua River and the stunning Cascade Mountains, residents enjoy a wealth of outdoor activities, from hiking and fishing to camping and bird-watching.

The town’s vibrant community spirit is evident in its local events and gatherings, which bring neighbors together throughout the year. Winchester boasts a variety of amenities, including cozy cafes, boutique shops, and parks that provide a perfect backdrop for family outings or peaceful afternoons. With easy access to larger cities like Roseburg, you can enjoy the tranquility of rural living while still being close to urban conveniences.

For those considering a move to this enchanting area, there are a variety of homes for sale in Winchester that cater to diverse tastes and budgets. Whether you’re looking for a charming cottage with a white picket fence, a spacious family home with expansive views, or a modern retreat surrounded by nature, you’re sure to find the perfect fit. Each property reflects the warmth and character of the community, making it easy to envision your life here.

Explore the homes for sale in Winchester, and discover the opportunity to create lasting memories in this delightful Oregon town. Embrace the lifestyle you’ve always dreamed of, and let Winchester welcome you home!

Newest Winchester Homes for Sale

$530,000

3 Beds ⋅ 2 Baths ⋅ 636742962 MLS

Charming and ideally located at 849 N View Dr, this home offers a seamless blend of comfort, functionality, and convenience. The thoughtfully designed layout features 3 bedrooms and 2 bathrooms with inviting living spaces bathed in natural light, creating a warm and welcoming atmosphere. Enjoy a fenced yard, sprinkler system, RV parking, and a garage, perfect for both relaxation and practicality. Nestled in a peaceful setting, yet just minutes from shopping, dining, local amenities, and major commuter routes, it combines tranquility with accessibility. Set in a highly desirable neighborhood, this property is a fantastic opportunity for both homeowners and investors—don’t miss your chance!

849 NORTH VIEW DR, Winchester

$485,000

3 Beds ⋅ 2 Baths ⋅ 176433898 MLS

Welcome to this beautifully updated residence in one of Winchester's sought-after neighborhoods. Nestled on a quiet, dead-end street with a welcoming atmosphere, this home offers the perfect blend of comfort, style, and convenience. Filled with natural light from expansive windows, the thoughtfully designed floor plan features 3 spacious bedrooms, including a luxurious primary suite with a stunning walk-in closet complete with custom built-in storage and a dedicated vanity. Quartz countertops, tiled showers, and tasteful updates throughout create a fresh, modern feel. Designed for today's lifestyle, the home also offers a versatile bonus room with French doors—ideal as a home office or potential 4th bedroom—plus an additional flex space perfect for a family room, game room, or media room. The well-appointed kitchen features abundant cabinetry, two pantry/storage closets. The layout of the home and living spaces, make entertaining effortless. Additional storage includes a coat closet, oversized linen closet, utility/storage room, and generous cabinetry in the laundry room. Step outside to enjoy the spacious front and backyard, offering plenty of room for gatherings, play, or simply relaxing. The garage features an epoxy-coated floor, and the attached shop provides additional workspace with a bank of cabinets or the potential to convert into a covered carport. Large driveway that can easily fit 6 vehicles. Ideal location--less than five minutes from I-5, approx 10 minutes to Umpqua Community College, and less than 1 mile from the beautiful North Umpqua River, where swimming, rafting, kayaking, and fishing can be enjoyed all summer long. If you have been searching for a move-in-ready home in a peaceful, established neighborhood with room to entertain and an unbeatable location, this Winchester gem is one you won't want to miss! More photos coming soon. Agent is owner.

339 PIONEER WAY, Winchester

$399,000

3 Beds ⋅ 2 Baths ⋅ 487961392 MLS

If you've been waiting for a home in Winchester with a great location and the chance to make it your own, this is one worth seeing. Just minutes from the North Umpqua River, Amacher Park, and I-5, you'll enjoy mountain views, a fenced backyard, and a new deck that's ready for summer evenings.The main level feels open and comfortable with a spacious living room, fireplace, and access to front and back decks. The primary suite is tucked away with vaulted ceilings, skylights, and a roomy tile bathroom, creating a quiet place to unwind. Downstairs adds even more flexibility with a family room warmed by a pellet stove, a half bath, laundry room with utility sink, and an oversized garage with plenty of storage.This home could use some fresh ideas and updating, but the location, layout, and setting make it an easy one to picture investing in. Bring your vision and build equity in a great neighborhood.

623 PIONEER WAY, Winchester

$489,500

4 Beds ⋅ 3 Baths ⋅ 271779634 MLS

Stunning custom built home in Winchester! Enjoy views of the North Umpqua River and bridge views from the large wrap-around deck. Inside features a grand great room, granite counters, an upgraded range, vinyl windows, new ductless HVAC, and built-in storage. Ideal for large or multi-family potential: downstairs offers extended living area, office, and play space. Outside, enjoy a huge yard with fruit trees, RV parking, and river access. Minutes to schools, shopping, and easy I-5 access. Schedule a tour today!

170 HURRICANE LN, Winchester

$615,000

4 Beds ⋅ 2 Baths ⋅ 277360378 MLS

This beautiful custom home is located in one of Douglas County's premier neighborhoods and there is no HOA! The all level lot is nearly 1/2 acre in size and boasts an amazing amount of parking. Bring your automobiles, RVs, boats, golf carts, trailers, or whatever you have, as there is room for all! The home's interior features a spacious kitchen with built in-oven and microwave, a downdraft gas range/oven, island, eating bar, dining nook, refrigerator with water and ice, disposal and tile flooring. The comfortable living room is centered around a classy gas fireplace and has a cathedral ceiling. The primary bedroom is good sized and has direct access to the back patio, (which would be a great place to install a hot tub), along with a bathroom with a walk-in shower, garden tub, double sink vanity and a walk-in closet. The den/office has 2 doors, with one being a french door. The family room makes a great spot to enjoy your favorite indoor activities. There is a formal dining room directly off the kitchen. The upper level is very unique and has two bedrooms. Enjoy the wonderful summer weather in the fully fenced expansive back and side yards, and on the covered patio on the rear of the home, which is accessible directly from the kitchen, making for great outdoor entertaining and living. In addition to all the parking in, and adjacent to the driveway, there is a lot of parking behind the gated fence on the right side of the home. Detached carport structure and storage shed are included. All this and low county taxes! If this sounds like a place you would enjoy calling yours, don't delay, call for a viewing appointment today!

251 MARTHA DR, Winchester

$549,000

4 Beds ⋅ 3 Baths ⋅ 414398974 MLS

Located in the highly desirable Winchester Creek community, this well-maintained 4-bedroom, 3-bath home offers approximately 2,954 sq. ft. of living space, an oversized 2-car garage, and rare neighborhood privacy. Bordered by protected open space on three sides, it enjoys a sense of separation with the sounds of Winchester Creek nearby. The exterior features stone masonry accents, mature Japanese maples, a picket-fenced lawn, and low-maintenance landscaping. Inside, the main level offers an open-concept great room with formal dining, granite countertops, hardwood and tile flooring, recessed lighting, a dedicated office, full guest bath, and a secondary bedroom for guests, nursery, or workspace. The primary suite includes a soaking tub, walk-in tile shower, and walk-in closet. Sliding doors off the kitchen open to an elevated deck overlooking greenery, extending the living area outdoors. The daylight lower level functions as a second living suite with a large family room, abundant natural light, and access to a second deck. Established honeysuckle adds seasonal color and fragrance. This level includes two bedrooms, a full bath, dedicated laundry room, and flexible space for gym, media room, hobby area, guest quarters, or additional bedroom use. With its own exterior entrance, it offers strong multigenerational living or income potential. Additional features include laundry hookups on both levels, waterproof vinyl flooring in key lower areas, a pet door, Tesla Level 2 charger on a dedicated 240V circuit, and included Samsung washer/dryer plus large-screen TV. Outdoor living includes a raised brick planter, secluded patio retreat, fenced backyard, Rain Bird drip irrigation system, and landscaped pathways. Conveniently located near the North Umpqua River, I-5, Costco, and medical facilities, this home offers space, flexibility, privacy, and low-maintenance living in one of North Roseburg’s most sought-after neighborhoods.

286 WINCHESTER CREEK AVE, Winchester

$499,000

4 Beds ⋅ 2 Baths ⋅ 152479269 MLS

Priced to sell and offering exceptional value in Winchester's sought-after Oak Valley Loop neighborhood! This beautifully maintained 4-bedroom, 2.5-bath home offers 2,581 square feet of thoughtfully designed living space, combining timeless finishes, everyday comfort, and room to grow.Step inside to soaring vaulted ceilings, rich bamboo flooring, and a warm natural gas fireplace that creates an inviting focal point in the main living area. The spacious main-level primary suite provides a private retreat, featuring a luxurious ensuite bath with a tiled walk-in shower, double vanity, relaxing jetted tub, and generous walk-in closet.Designed with both entertaining and daily living in mind, the kitchen showcases granite countertops, stainless steel appliances, under-cabinet lighting, a walk-in pantry, and an eating bar that seamlessly connects to the formal dining area. Step outside to the deck and enjoy effortless indoor-outdoor living, perfect for summer barbecues, morning coffee, or evening gatherings.Upstairs, a versatile bonus loft offers additional living space, while three generously sized bedrooms—each with its own walk-in closet—provide comfort and flexibility for family, guests, hobbies, or a home office.An extra-deep two-car garage, abundant storage throughout, fresh interior and exterior paint, and mature landscaping add to the home's appeal. The fully fenced backyard creates a private outdoor oasis, offering plenty of space to relax, garden, or play.With a Real Market Value of $593,570, this home presents an incredible opportunity to own in one of Winchester's most desirable neighborhoods. Conveniently located near schools, shopping, and recreation, 556 N View Drive delivers the perfect blend of space, quality, and value. Schedule your private tour today!

556 NORTH VIEW DR, Winchester

$519,900

3 Beds ⋅ 2 Baths ⋅ 190207928 MLS

Lower taxes in the Winchester area, outside the city limits! Home is all on one level! This quality-crafted home offers comfort, space, and exceptional curb appeal on a large corner lot. Featuring 3 bedrooms and 2 bathrooms, the thoughtfully designed floor plan combines functionality with timeless style. Inside, you’ll find soaring high ceilings that create an airy, inviting atmosphere, along with a dedicated office behind elegant French doors — perfect for working from home or a quiet retreat. The spacious kitchen offers abundant cabinetry, a convenient eating bar, and flows seamlessly into both the formal dining room and a cozy breakfast nook for everyday living. The private primary ensuite is designed for relaxation with granite countertops, double sinks, and a generous walk-in closet. Outside, the beautifully landscaped yard is filled with mature plantings and trees, creating a peaceful setting to enjoy from the covered rear patio. A circular driveway provides easy access and impressive curb appeal, while the private RV parking tucked behind the home offers added convenience and flexibility. A storage shed adds extra room for tools, hobbies, or seasonal storage. New roof in 2025. This well-appointed property combines comfort, privacy, and charm in one of Winchester’s desirable, most sought-after locations.

147 WINGFOOT CT, Winchester

$489,000

3 Beds ⋅ 3 Baths ⋅ 668222765 MLS

Beautifully updated Winchester home with approximately $80K in recent upgrades, offering flexible living options and move-in ready comfort. This charming single-level home sits on a spacious level,lot features a fully remodeled kitchen, new fixtures throughout,new flooring throuout including hickory engineered harwood, remolded master suite, new laundry room, new ductless heating/cooling,new tankless H2o tank, and a cozy gas fireplace insert. Two bonus rooms connected by a breezeway provides an ideal office, hobby room, or flex space, or added storage room adds even more utility. The property includes a carport, ample driveway parking, and a separate garage with its own laundry. Above the garage is a fully furnished 1BD/1BA guest studio—perfect for extended family, guests, or potential rental income. The expansive fully fenced backyard offers room for gardening, play, or projects, complete with a workshop and greenhouse for year-round gardening. Additional improvements include a new roof installed in 2023 and fresh interior and exterior paint. This super-cute property offers privacy, versatility, and excellent multi-use living options in a peaceful Winchester setting. Truly move-in ready and charming.

335 PAGE RD, Winchester

$415,000

3 Beds ⋅ 2 Baths ⋅ 317509469 MLS

Top location in subdivision for view of the pond and greenbelt. Fenced with back deck. Common area tennis court, playground and walking trail. This lovely 2001 built home has vaulted ceilings, 3 bedrooms, 2 baths 1427 sq ft. Recently upgraded remodeled kitchen with breakfast nook, both baths totally remodeled, and flooring upgraded. Quartz countertops, new sink, newly painted interior. Great floor plan with spacious double garage. Sprinkler system. Seller will install new roof. Covered porch in back yard overlooking pond. Great outdoor space. Move in ready!

260 VILLAGE DR, Winchester

$599,000

3 Beds ⋅ 2 Baths ⋅ 739910850 MLS

Welcome to 411 Oak Valley Loop, a meticulously maintained custom home offering single-level living, quality craftsmanship, and exceptional comfort in one of Winchester’s desirable neighborhoods. This beautiful 3-bedroom, 2.5-bath residence offers 2,361 square feet of thoughtfully designed living space with minimal steps, making everyday living both convenient and accessible. Rich bamboo flooring, tile accents, and abundant natural light create a warm and inviting atmosphere throughout.At the heart of the home, the spacious kitchen is designed for gathering and entertaining, featuring granite countertops, a 5-burner gas range, stainless steel appliances, pantry storage, and ample workspace. The adjoining great room offers a cozy gas fireplace and sliding glass door that opens to the covered patio, creating a seamless indoor-outdoor living experience.The spacious primary suite provides a private retreat with dual closets, including a walk-in closet, double-sink vanity, and direct access to the back yard through a sliding glass door. Two additional bedrooms are connected by a convenient shared bath, while a charming bay window in one adds character and natural light to the home.Outside, you’ll find a beautifully landscaped and fully fenced backyard designed for privacy and relaxation. Whether enjoying your morning coffee on the covered patio or entertaining guests, this outdoor space is sure to impress.Car enthusiasts, hobbyists, and those needing extra storage will appreciate the oversized 3-car garage with pull-through access to the backyard, along with abundant additional parking.Combining timeless style, pride of ownership, and functional living spaces, this move-in-ready custom home is a rare opportunity to enjoy the very best of Douglas County living. Call for your private tour today!

411 OAK VALLEY LOOP, Winchester

$999,000

4 Beds ⋅ 2 Baths ⋅ 786977472 MLS

Tucked away in one of Douglas County's most desirable neighborhoods, this stunning 19th century inspired custom Haynes-built home is a true showstopper. This 3,774 sq ft residence offers 4 bedrooms, 2.5 baths on a private, beautifully landscaped .63-acre lot.Step into a grand entry with soaring ceilings extending into the living and dining rooms, highlighted by 10-inch crown molding and hardwood floors with elegant mahogany inlay. The living room features a gas fireplace, while the family room offers a cozy wood stove. Decorative ornamental plaster adds timeless character to the living room and primary suite.The chef’s kitchen is designed for both function and style, featuring granite countertops, a large butcher block island with eating bar, gas cooktop, double ovens, custom built-in refrigerator, garden window, butler’s pantry, and additional pantry. Custom cabinetry throughout is inspired by Smallbone English design. The primary suite is a private retreat with French doors to its own deck, and a luxurious bath with Italian marble, jetted tub, and walk-in shower. A dedicated office showcases beautiful woodwork, hardwood floors, and built-ins.Outside, enjoy a large entertaining deck, gazebo, potting shed, and a peaceful seasonal creek. The exterior features reclaimed brick from the historic Umpqua Hotel, adding unique character.The impressive shop includes a 5-foot pit, loft “man cave,” and half bath—perfect for hobbies or storage. Community amenities include a swimming pool and tennis court.A rare blend of craftsmanship, history, and luxury—schedule your private tour today.

539 WILD FERN DR, Winchester

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The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.